Ah…the stress, the miscommunication, the insecurity, the jealousy, the anger—who wouldn’t want to double up on dating? Okay, there are good things about dating two people, too. There’s variety, excitement, double the sex…Well really, we don’t need to look much further than that to find a reason, do we?

When you’re dating, there is often a vagueness to just how committed a relationship is, so it’s not at all uncommon to find yourself getting serious with one partner while you still have one or more other people that you are seeing regularly. This can lead you to the point where you have to make the critical decision whether to go to just one relationship or keep dating two people.

Can you afford to date two people?

Dating costs money, especially for men. Most men lament that they can’t afford to date one woman, much less spring for drinks, food, activities, and gifts for two. And if they know about each other and one finds out that you’re spending less on her than the other one—good luck!

Women have their financial challenges in dating, too. Hair, makeup, clothes, shoes, purses—all of these things add to “the look” when you go out, and all of them add up. They add up twice as fast when you’re dating two guys. The insult to injury is that both guys together probably won’t notice half of the effort you put into looking beautiful for them.

Is there enough of you to go around?

No, we’re not talking about weight here, although if all of your dates are nice dinners you’ll pack on the pounds pretty quickly when you’re dating two people. What we’re really talking about is time, attention, and affection. Honestly, a lot of people don’t have enough time, attention, and affection for one relationship, much less two.

If you think about the average person you date, even if you only see them once or twice a week, that’s usually about three to ten hours a week of commitment when you figure in the time to get ready, drive time, and so on. Add on to that the phone calls, texts, emails, and time spent buying gifts or pondering just what the heck the deal is with the person you’re dating, and you’ve got quite a time commitment. Now imagine doubling that if you’re thinking of dating two people.

How will your dates react if they find out about each other?

If you’re in a committed dating relationship, or even if the person you’re dating thinks you’re in a committed dating relationship, you’re going to need to keep your other dating activity secret. If you fail to do this, your dates’ reaction might be the type of dramatic eruption that gets you some time on daytime talk shows, and nobody wants that. Keeping your dates from finding out about each other creates a pretty stressful situation that will increase the amount of time and emotional stress you spend on each relationship.

If you’re in the early stages of dating or if you have a truly free and open relationship, you might think you have nothing to worry about if one date finds out about the other. Don’t count on it. People are people, and when a person finds out that their date is dating someone else, it often leads to jealousy, insecurity, and competitive feelings that can get very ugly, very fast, in most cases.

Still, it doesn’t have to be that way. Once in a while you’ll find that you’re dating a truly open-minded free spirit who is absolutely fine with you dating other people, and maybe even encourages it. Do you dare say “threesome?”

What is your ultimate goal?

Most people, whether they realize it or not, enter a dating situation with a plan. In many cases, they are looking for “the one”–the person who they will be with for the rest of their lives. If this is your goal, then maybe you should be a little more hesitant about dating multiple people because you might find yourself trying to sort out which of “the two” is “the one” and you might mess the whole thing up and end up with “the none.”

If your goal is to date as many people as you want and just have fun, it will be a lot easier to make an argument for dating two people at the same time. As long as you’re not misleading them and you’re pretty sure that neither of them is making wedding plans while you’re carving notches in your headboard, it’s all good.

One thing to beware of is that goals do change as you progress through dating relationships, and the date that started out as a booty call might well start to look like the love of your life. This can be problematic if you are dating two people, as your feelings might get stronger for either of the people you’re dating, or even both. This often forces you to make a sometimes painful choice about who you will continue to see and who gets left behind.

If dating one person is fun, dating two should be twice as fun, right? Maybe, if you really have the time and money to support two relationships, if your dating partners are accepting of it, and the whole situation fits in with your relationship goals. If all of these things aren’t right, good luck—you’ll need it.

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